4-Bromobiphenyl → N-(3,5-Dimethylphenyl)-N-(4-phenylphenyl)benzophenone hydrazone

HRID 1978281

Reaktionsgleichung

Reaktionsgleichung von HRID 1978281
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][N:10]=[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.Br[C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:27][CH:26]=1.CC([O-])(C)C.[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[CH3:8][C:6]1[CH:5]=[C:4]([N:9]([C:34]2[CH:35]=[CH:36][C:31]([C:28]3[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=3)=[CH:32][CH:33]=2)[N:10]=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:3]=[C:2]([CH3:1])[CH:7]=1

Komponenten

6

Edukt 3

HCID 71014-BromobiphenylHCID 207408531-(3,5-Dimethylphenyl)-2-(diphenylmethylene)hydrazineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 12081749N-(3,5-Dimethylphenyl)-N-(4-phenylphenyl)benzophenone hydrazoneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

N-(3,5-Dimethylphenyl)benzophenone hydrazone (1.0 equiv., 0.5 mmol, 150 mg), 4-bromobiphenyl (1.0 equiv., 0.5 mmol, 117 mg), Pd(OAc)2 (0.01 equiv, 0.005 mmol, 2 mg), DPE-phos (0.01 equiv, 0.005 mmol, 3 mg), and toluene (1 mL) were added to an oven dried test tube and stirred at room temperature for 2 minutes. NaOtBu (1.4 equiv., 0.7 mmol, 67 mg) and an additional 1 mL toluene were then added. The test tube was then capped with a septum, briefly purged with argon (˜1 min.) and then heated to 100° C. under argon for 14 hours. The reaction solution was then cooled to room temperature, diluted with Et2O, filtered through Celite, and concentrated under vacuum to give the crude product as a brown oil. Purification by flash column chromatography (2% EtOAc/Hex) gave the title product as a yellow solid (149 mg, 0.33 mmol, 66% yield).

Aufarbeitung

  1. customdried test tube
  2. customThe test tube was then capped with a septum
  3. custombriefly purged with argon (˜1 min.)
  4. temperatureheated to 100° C. under argon for 14 hours
  5. temperatureThe reaction solution was then cooled to room temperature
  6. additiondiluted with Et2O
  7. filtrationfiltered through Celite
  8. concentrationconcentrated under vacuum
  9. customto give the crude product as a brown oil
  10. customPurification by flash column chromatography (2% EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-5949e4fa05864e4fbe68b1953c2b35cf
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235936B1

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